Ruthenium-catalyzed cyclization of ketoxime acetates with DMF for synthesis of symmetrical pyridines.

Org Lett

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an 710069, P. R. China.

Published: June 2014

A novel ruthenium-catalyzed cyclization of ketoxime carboxylates with N,N-dimethylformamide (DMF) for the synthesis of tetrasubstituted symmetrical pyridines has been developed. A methyl carbon on DMF performed as a source of a one carbon synthon. And NaHSO3 plays a role in the reaction.

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol501183zDOI Listing

Publication Analysis

Top Keywords

ruthenium-catalyzed cyclization
8
cyclization ketoxime
8
dmf synthesis
8
symmetrical pyridines
8
ketoxime acetates
4
acetates dmf
4
synthesis symmetrical
4
pyridines novel
4
novel ruthenium-catalyzed
4
ketoxime carboxylates
4

Similar Publications

A ruthenium-catalyzed intramolecular cascade cyclization of allene-alkyne has been achieved. This method offers a streamlined and atom-economical approach for the construction of sulfone bearing 1-cyclopenta[]naphthalenes, an important structural scaffold that exists in biologically active compounds. Our approach, backed by mechanistic insights from deuterium labeling, DFT calculations, and potential for reaction scale-up, presents synthetic chemists with an invaluable tool for efficiently producing a distinct carbon framework in a one-pot manner.

View Article and Find Full Text PDF

Quinazolinone-to-Isoquinoline Metamorphosis by Ruthenium-Catalyzed [4+2] Annulation with Sulfoxonium Ylides.

Org Lett

December 2024

Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States.

Molecular editing of quinazolinones to isoquinolines by a novel ruthenium-catalyzed [4+2] annulation with sulfoxonium ylides has been developed. The method permits the precise and rapid assembly of multisubstituted aminoisoquinolines, a class of heterocycles that play a privileged role in organic synthesis and pharmaceutical development. This new catalytic process exhibits novel programmability, including directed C-H acetylation, nucleophilic cyclization, and alcoholysis.

View Article and Find Full Text PDF

Mechanistic Investigation of a Photoredox Cycloaddition Chain Reaction.

J Am Chem Soc

December 2024

Department of Chemistry, Binghamton University, Binghamton, New York 13902, United States.

Photoredox catalysis is important in modern organic chemistry and the development of new synthetic methods. Mechanistic insights, particularly with photoredox chain reactions, are underdeveloped. This study combines quantum yield (QY) measurements, transient absorption spectroscopy (TAS), and electrochemical analysis to rigorously characterize the mechanism and rate constants of a ruthenium-catalyzed photoredox chain [4 + 2] cyclization between -anethole and isoprene.

View Article and Find Full Text PDF

A simple and efficient method has been developed for the synthesis of a diverse range of aryl-fused indolizin-3-ones through sequential Au(I)-catalyzed hydrocarboxylation, aminolysis, and cyclization, followed by ruthenium-catalyzed ring-closing metathesis. Moderate to good yields were observed with satisfactory substrate scope and functional group tolerance. The developed protocol represents a practical strategy for the construction of bioactive aryl-fused indolizin-3-ones.

View Article and Find Full Text PDF

Synthesis of silyl indenes by ruthenium-catalyzed aldehyde- and acylsilane-enabled C-H alkylation/cyclization.

Org Biomol Chem

January 2024

College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, 311121 Zhejiang, China.

A ruthenium-catalyzed C-H alkylation/cyclization sequence is presented to prepare silyl indenes with atom and step-economy. This domino reaction is triggered by acyl silane-directed C-H activation, and an aldehyde controlled the following enol cyclization/condensation other than β-H elimination. The protocol tolerates a broad substitution pattern, and the further synthetic elaboration of silyl indenes allows access to a diverse range of interesting indene and indanone derivatives.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!